Making It Up As We Go
by castielsunicorn
Summary: From the surface, it looks like Castiel Novak has everything going for him. He has a beautiful apartment in downtown Manhattan with his fiancé Meg; he is a successful businessman at the young age of 23, and is pretty easy on the eyes. , Castiel has the perfect life...until he met Dean and realized he was right...he wasn't a heterosexual man. (Destiel fanfic)
1. Chapter 1

Hi everyone! This is the first Supernatural fanfic I've written! It's also a destiel fanfic so if you're not into that then you won't like this. I know it's flawed and is kinda messy but it's my first try in a long time. I hope you enjoy! =)

Castiel walked into the bar with his brother Gabriel, feeling so nervous and annoyed that his brother dragged him here. He wouldn't have minded if it was any other bar but it was a gay bar. He had recently told his brother that even though he was engaged to his college girlfriend, Meg, he couldn't help but feel that something was wrong since he was in high school and he might be gay. His brother being the only reasonable person in his family, he felt comfortable telling him and Gabe wanted to help his little brother out. They grew up religious and Castiel felt obligated to get a girlfriend in college then propose to her when they graduated. When they found two stools available at the bar, they sat down. When the bartender came around to ask them for their order Castiel froze. The bartender looked into Castiel's eyes with his deep green eyes and smiled. Castiel couldn't look away and the bartender waved his hand in his face after Castiel ignored his question.

"Yes?" Castiel finally responded

"What can I get you to drink handsome?" The bartender replied with a smirk

Castiel blushes and said "Um just a gin and tonic please"

"Same for me please!" Gabriel said.

"You got it," the bartender said while smiling.

"You are definitely gay Cassie" whispered Gabe.

"Now why would you say that?" Hissed Castiel

"HMM because you can't stop staring at the bartenders ass!" Gabe said while giggling.

"Shut up! No I'm not!" Castiel blushed

"Yes you are! Now, I see a lady all by herself and that's my queue to let you do your thing" gabe laughed

"No no no I don't even know what the thing is!" Castiel whispered

The bartender walked back with their drinks. Gabe took his drink and said "Well you're gonna find out! Have fun Cassie!" and walked away.

"Dammit" Castiel whispered to himself.

"So your name is Cassie?" The bartender asked with a smirk.

"Um no, my brother likes to call me that." Castiel grumbled. "My name is Castiel."

"Castiel? Hm I like that." The bartender smiled "I'm Dean."

"Hello Dean." Castiel said

"So what brings you here with your brother?" Dean questioned

"Well, it's a long story. One that I'm sure someone like you is not interested in."

Dean looked into Castiel's blue eyes and could see all of the years of confusion and pain.

Dean smirked at him and with a deep voice said, "Try me, Cas."

Castiel raised his eyebrows at him when he called him Cas. No one has ever called him that before. He was starting to feel that feeling when he would stare at an attractive guy for too long and he started getting nervous.

"Um, m-maybe some other time." Castiel stuttered. He downed his drink and ran out of the bar.

_WHAT THE HELL WAS THAT!? _Cas thought to himself.

_No no no no I can't be…I can't be gay. FUCK. SHIT FUCK. What would my family think? What would my friends think? What would Meg think…?_

Castiel ran up the block and leaned against a brick wall. He slid down and buried his face in his hands.

"Cassie what the hell!" Gabe shouts while running towards Cas.

"I'm gay. GABE I'M GAY. MY LIFE IS RUINED!" Cas screams while kicking the wall.

"Cassie it's not ruined. It's not that big of a deal!" Gab said.

"Gabe, our family is going to be disappointed and I'm getting married in THREE MONTHS. THREE FUCKING MONTHS! AND I AM NOT EVEN SEXUALLY ATTRACTED TO MY FIANCE!" Cas starts sobbing into Gabe's shoulder.

"Hey Cassie no don't cry" Gabe says while trying to soothe his brother.

"Gabe, what am I going to do?"

"Cassie, we are going to figure this out. You deserve to be happy but the first thing you have to do is tell Meg." Gabe said

"Oh no I cant do that. Maybe I should see a therapist or something." muttered Cas.

"Don't be crazy. There is nothing wrong with you. It's not going to be easy but you can't keep lying to yourself anymore." Gabe said while rubbing his arm.

"You're right Gabe. I just want to go home." Castiel sighed.

Just as they got into the cab and the cab took off, Dean came running outside.

"HEY CAS YOU FORGOT YOUR WALLET!" Dean shouted.

To Be Continued...


	2. Chapter 2

Castiel and Gabe didn't even notice Dean.

Dean stood there on the street with Castiel's wallet in his hand, trying to figure out what to do. Dean stared at it until he opened it and took out his license. He saw his address and realized it wasn't too far away by cab. He could get in a cab and give it to him right now but he wanted to see him during the day. There was something about this guy that was different than the other insecure men that he deals with on a daily basis. He wanted to find out more about him. He looked into his wallet and found his business card with his work address on it.

_::I'll stop by his office tomorrow give it to him then.:: _Dean thought.

Dean was feeling nervous and he didn't understand why. He's so secure in his sexuality and who he is and he never gets nervous around a guy that he's attracted to but with Castiel it's different. He barely even knew the guy! Dean went back into the bar and finished his shift before he went home.

When Dean arrived at his apartment that night, he couldn't help but think of Castiel. He was getting annoyed with himself because he's Dean Fucking Winchester. He doesn't let any guy make him linger around in his head. Not since…Ash. Ash was the only guy he let into his heart. He torn down his walls and let him in. He wasn't until he caught Ash with another guy in their apartment, in their bed. That destroyed him. That was the day that he built those walls sky high and never let anyone in again.

He didn't understand why this guy that he barely knew was getting to him. He couldn't help but be intrigued by his innocence and those gorgeous blue eyes. God he could be lost in those eyes for days. The more he thought about those eyes and the small smile Cas gave him and the way his stubble goes down his neck and how perfect his bone structure is…the more hard he grew in his boxer briefs. He groaned as he felt the pressure in his underwear. He stroked it through the underwear before he finally tore them off and started stroking himself. He thought of how his pretty pink lips would feel around his neck, around his own lips, and around his throbbing cock. He thought of Cas's sexy black messy hair and how he would sound if he tugged at it while he was fucking him from behind. His stroking was getting faster and rougher, moaning Cas' name out loud. He thought about how gorgeous he would look swallowing his own come and that was it, Dean screamed out Cas' name and came all over his hand and body. He was panting hard and couldn't believe he just jacked off thinking of Castiel. He cleaned himself off and went to bed.

The cab driver dropped off Castiel first.

"Thanks for tonight Gabriel. I appreciate it."

"Anytime bro! Also cab fare is on you next time!" Gabe smirked

"Of course. Thanks again." Castiel shut the cab door and went upstairs to his apartment.

He was feeling so confused. He is attracted to Dean. There. He could finally admit to himself that he is attracted to men. He just had to figure out how to incorporate this into his life so he can finally be happy. The first step was to tell his fiancé. He will worry about tomorrow. For now, he just wants to go bed. As he lays in bed, all he could think about was Dean. He was just some bartender but there was something about the way his smiled curved and how he said, "Try me, Cas." Like he was trying to seduce him right in that bar. It was so hot to him. He felt himself getting hard. He moaned as he touched it through his pajama pants but resists the urge. This was new to him and he was still trying to get use to it. He flipped on his stomach to try to ignore it. He thought it would help but it only made things worse. The fabric felt to good against his hard member as he rubbed up and down. He said, "Fuck it" and took off his pants. He started rubbing himself fast and hard as he thought about how good it would feel if Dean was there, kissing him fiercely, forcing his tongue in his mouth and down his throat. Cas started moaning loudly. All he wanted was Dean to put his lips on his cock and deep throat him. Cas moaned for Dean as his orgasm went through him and he poured himself all over his stomach. Cas felt so ashamed but he just didn't care. Cas cleaned himself up and fell asleep.

The next morning Cas woke up to a kiss from Meg.

"Hey sleepy head how was your night?" Meg said while getting undressed.

Meg was a nurse who worked night shifts at a hospital so she was just getting home as Castiel was leaving for work.

"Oh um it was okay, nothing eventful." Castiel said awkwardly.

"I'm so tired, I'm gonna shower then go to sleep. You should join me." Meg kissed Castiel then took the rest of her clothes off. She stood there naked, trying to give Castiel a hint that she wanted company in the shower. He always felt awkward because she had a beautiful body but he just wasn't attracted to it. It felt so wrong.

"Oh um thanks Meg. Maybe another time" Cas quickly kissed her cheek and walked out of their bedroom.

She sighed in frustration and walked into their master bathroom. She knows that he's stressed out from work but he never wants to have sex. It's like he only wants to have sex when he's had too much to drink, which is rare. She loves Castiel so she continued to ignore the problem.

Castiel made a pot of coffee right before he went to shower in the other bathroom. He took a quick shower and got dressed. He poured himself coffee in his to-go coffee cup, put on his trench coat, and left his apartment. When he walked into his office, he sat down and immediately got to work. His work was the only thing that got his mind off of what was going on in his life, which probably why is so successful for his age. He puts 100% of himself into his work.

Around noon, he excuses himself for lunch. When he left the building to get lunch, he noticed the same pair of green eyes from last night staring at him.

"Hey Cas." Dean smiled.

"Hello Dean…what are you doing here? Wait how did you know-"

"You forgot your wallet at the bar last night and I found your business card in it. It had your work address in it."

Cas checked his trench coat pockets and felt that they were both empty. He completely forgot about his wallet. He automatically thought it was in trench coat. He stared and Dean and took his wallet.

"Um, thank you Dean, that was really nice of you." Cas said awkwardly.

"Of course Cas." Dean said.

"Hey um," Cas started to say.

::_Oh my god what are you about to do Castiel. DON'T SAY IT DON'T SAY IT DON'T SAY IT.::_

"I'm getting some lunch, would you like to join me?" Castiel said while tripping over his words.

_::YOU IDIOT WHAT IF HE SAYS NO. WHY WOULD HE BE INTO SOMEONE LIKE YOU! DON'T FORGET YOU'RE STILL ENGAGED! WHAT THE HELL CASTIEL!::_

"I would love to, Cas." Dean smiled.

Sorry to end it there! I'm working on chapter 3 now so that should be up shortly. Also sorry these aren't the longest. I'm still working on how to divide these chapters up.

Thank you for reading and reviews are appreciated! =)


	3. Chapter 3

Castiel couldn't believe Dean said yes to lunch with him. Castel shyly smiled at him and they both walked side by side to get lunch. The walk was quiet. They both kind of felt awkward since they both had intense orgasms last night thinking of each other. The walk consisted of quick glances back and forth and some serious blushing from Castiel. Dean just smirked whenever Castiel blushed. He thought it was adorable. Dean thought everything about Castiel was adorable. He loved his gorgeous unruly bed hair, his slightly chapped pink lips, and his beautiful deep blue eyes that made his heart flutter whenever they made eye contact. Dean couldn't take the silence anymore and finally broke the ice.

"So how's your day going?" Dean asked while clearing his throat.

"It's okay. Getting better though." Castiel said shyly.

Dean couldn't help but just smile at him. "Well I'm glad, same here." Dean said warmly "So where are we going?"

"I was just going to get a soup and salad from this place but we can go somewhere else if you want."

Dean just stared at Castiel in disbelief. "Soup and salad? Who are you my brother? That is not real food. Let's go to Shake Shack! My treat." Dean said while grabbing Castiel's hand and leading the way. Castiel immediately got chills when Dean grabbed his hand. He couldn't help but feel that this just felt…_right._ He let a small smile form on his face and let Dean lead the way.

When they finally got to Shake Shack, Castiel let Dean order for him since he didn't know what was the best thing to get. Dean ordered them both two double smokeshack burgers with cheese fries and a soda. Dean carried their food to one of the open tables and sat down.

"Thank you Dean. This is…really nice." Castiel smiled

Dean loved it when he smiled. He didn't smile much at the bar last night so it was nice to see him show off those pearly whites. "No problem Cas." Dean took a bite of his burger and let out a low moan at how delicious it is. Cas heard him moan and couldn't help but get slightly aroused. Damn did he look attractive eating that burger.

"My god do I love this place." Dean continued digging into his burger as Cas finally took at bite of his and understood why Dean moaned.

"Dean, this is so delicious. I can't remember the last time I had a burger." Cas smiled as he continued to eat. Meg didn't really let him food that was unhealthy.

"Cas, you need to live a little. This is heaven." Dean mumbled with his mouth full. "So Cas, since I bought lunch, you have to tell me more about you."

Cas swallowed a piece of his burger and said, "Well…what do you want to know?" Cas started to feel nervous.

"For starters, why did you run out of the bar last night?" Dean stared into Castiel eyes, which made him even more nervous.

Castiel took a sip of his soda, trying to find an appropriate answer for Dean. Should he tell the truth? Lie?

Castiel sighed. "Well-"

"The truth Cas, please. Don't forget, this is 'some other time'" Dean smirked.

Castiel blushed at his smirk. "Well, honestly?"

Dean nodded.

"I just…I was scared of how attracted I am to you. I'm not really out of the closet. I guess I always knew I wasn't straight but I tried to ignore it. Push it down. I was ready to continue to ignore it but then I saw you behind that bar and realized I can't lie to myself anymore. I am what I am. The only person that knows it my brother Gabriel, and that is why be brought me to that bar. That was his way of being supportive." Castiel managed to get out. He looked down at the table, not wanting to see Dean's reaction.

Dean just stared at him. He knew he was telling the truth and felt horrible that he couldn't be himself. Dean reached across the table and lifted Castiel's head up. He looked deep into Castiel's damp eyes and said "Cas, its okay. I understand. I can help you out with this if you want." Dean smiled at him and just wanted to bad to lean over the table and claim his lips in a kiss but he resisted.

"Thanks Dean. I do have to get back to work though." Castiel said while looking at his watch.

"Of course. Ill walk you back." Dean got up, threw out their garbage and walked Castiel back to his office.

When they arrived at his building, Dean gave Castiel his phone number. "I have yours from your business card so I think it would be good if you had mine."

"Thanks Dean." Castiel gave a small smile.

They stared at each other for a few seconds before Dean pulled him in for a hug. He loved the feel of Castiel in his arms. He was only slightly less muscular than Dean but he still felt his pecks against his chest. He wishes that he could feel it while they were both shirtless. Dean let go of Castiel and Cas started walking into his building. Before he entered he heard Dean say, "Hey Cas?"

Castiel turned around looking confused and said "Yes Dean?"

Dean smirked and said, "I'm scared of how attracted I am to you too."

Castiel stared at him with wide eyes as he watched Dean walk away.

* * *

When Castiel got back to his office, he couldn't wipe the grin off of his face. Dean thought he was attractive too.

Castiel finished up the rest of his work and finished earlier than he expected. He was about to head home early when his office phone rang.

"Castiel Novak."

"Hey baby how's your day?"

Shit. It was Meg. He actually completely forgot about her. How could he forget was suppose to be getting married to this woman in three months!? Oh yeah because he was distracted by the beautiful bowlegged man with the green eyes.

"It's fine. How's yours?" Castiel muttered.

"It's going well. I have the night off and I thought it would be good for us to have dinner tonight. It's been awhile." Meg said.

Castiel knew what she meant by _it's been awhile. _She wasn't talking about dinner. Just as he was about to say "sure", he cell phone buzzed. It was a number he didn't recognize but knew who it was when he saw the message.

**Hey Cas, I know we just saw each other but I have the night off tonight. Wanna meet me at my apartment at 7 and get a drink? I still wanna know more about you. ;)**

Castiel stared at his phone and groaned. He knew whom he wanted to see more.

"Castiel? You there?"

"Yeah. Listen honey, I can't tonight. I have to work late and afterwards I promised Gabriel I would hang out." Castiel lied. He hated lying but he wanted to see Dean again.

"But tonight was the only night I had off and I really wanted to spend it with you." Castiel could hear the annoyance in her voice but stuck with his plan.

"How about I take you to brunch on Sunday? I know you only have off on Thursdays and Sundays." Castiel compromised.

"That sounds great. I'll be home by 6 if you change your mind. Love you." Meg said while hanging up.

Castiel sighed in relief and texted Dean back.

**Hello Dean, I'd love to. Text me your address and I'll see you at 7.**

Castiel was so excited. He couldn't wait to see Dean again. He got up from his chair and left his office to go home and get ready before Meg came home. On his way out he figured he would call Gabriel to tell him what he was up to incase Meg called him. Gabriel picked up on the third ring.

"Hey Cassie! How's it going?" Gabriel said eagerly.

"Hey Gabriel. It's going well. Um, I need to ask you for a favor."

"What does your heart desire baby bro?"

Castiel was silent for a moment before cleared his throat and said, "Well, remember the bartender from the bar we went to last night?"

Gabriel thought for a moment and shouted"Oh yeah! The green eyed man that you totally had the hots for." Gabriel snickered.

Castiel rolled his eyes but he was right. "Shut up Gabriel. Well anyways, I'm hanging out with him tonight but I told Meg that I'm hanging out with you so if she calls can you-" Castiel was interrupted by his brother.

"Say no more baby bro, I got your back. I do expect you to call me afterwards with the deets!"

Castiel sighed. "Fine Gabriel. I will call you afterwards."

"Awesome. Have you decided what to do about your wedding? Are you going to cancel it?" Gabriel asked.

"I…I don't know. I just have to see what this thing with Dean is first. I'll call you later." Castiel hung up the phone. He didn't want to think about his wedding or anything else besides Dean. Castiel left his building and headed home to get ready for his date with Dean.

* * *

Hi all! Sorry this is short and that this took awhile. I haven't had a lot of time to write. I'm going to try to at least write half of chapter 4 before I go to bed and finish up chapter 3 of When I Wake I Will Have To Slip Away. I hope you guys enjoy! If you did, reviews are nice =)


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